I Won't Let You Die a Virgin
by Aruuuu
Summary: "Well it's your last night on earth…What are your plans?"..."I just thought I'd sit here quietly" the angel replied completely serious. Dean/Castiel. Complete!
1. I Won't Let You Die A Virgin

**Story:** I Won't Let You Die a Virgin  
**Author: **Aruuuu  
**Disclaimer:** I DO NOT own Supernatural, I am merely writing out of pure fun hahaa.

**NOTE: **Season 5(spoilers?) The beginning was taken directly from the 4th episode. Most of the dialogue is correct. A few errors here and there because I did it from memory.

ALSO. I AM BACK BABYY :] Got my mojo back recently and I'm trying to adapt to my new style of writing. It's changed some over the years I've been gone

Enjoy the dream I had a few nights ago hahaha.

* * *

"Well it's your last night on earth…What are your plans?"

"I just thought I'd sit here quietly" the angel replied completely serious.

"Dude common…anything? Hmm? Booze… Women…anything?" the oldest Winchester raised his brows waiting for an answer from the angel. The angel diverted his eyes from the human at the word women, slightly embarrassed.

"…You have been with women before, right? Or an angel at least?" Dean questioned as the angel proceeded to rub the back of his neck nervously.

"You mean to tell me you've never been up there doing a little cloud seeding?"

"I've never had an occasion, okay?" the angel responded quickly.

Dean paused in disbelief at what the angel had said.

"Alright. There are two things that I know for certain. One. Burt and Earnie are gay. Two. You are not going to die a virgin. Not on my watch. Let's go."

Castiel hesitated as he followed the hunter into the bar. Dean strolled right in like he did this every day. He walked over to an open table, gesturing to Castiel to sit down. The angel's eyes darted back and forth, side to side, scanning the room and all the people in it. He swallowed in nervousness as all kinds of women walked by.

"Hey, what's your name?" a voice whispered into his ear. Castiel had no idea how to react. He gave Dean a nervous and perplexed look as if pleading for help.

"It's Cas. His name is Cas." Dean smirked looking at the woman who had wrapped her arm around the angel's shoulder. "What's yours?"

"Chastity" she smiled.

Dean couldn't help but snicker at the girl's name. "Chastity?" he repeated in a humorous way.

"I'll show you a good time" the woman giggled pulling Castiel to his feet and dragging him toward the back room. Again the poor defenseless angel pleaded for Dean's help. The hunter could only smile and laugh, handing Castiel a wad of cash, watching him get dragged to the back room.

It had only been about five minutes since Castiel had gone off with Chastity, when the shrill shriek of a woman ran through the halls of the hooker bar.

Dean quickly made his way to the end of the hallway where the rooms were hidden from the bar. A very agitated and horrified Chastity was scrambling away from the half undressed angel standing in front of the room they had entered.

"Screw you asshole! Screw you too!!" she screamed at Dean who had not registered what had just happened. She pushed her way out of the hall and out of sight.

"What the hell did you do to her?" Dean was trying his best to hide his amusement.

The angel tilted his head in confusion before speaking. "I merely looked into her eyes and told her it was not her fault that her father, Gene, had run out on her. He just hated his job at the post office."

Dean could not hold his laughed in, "dude, this whole industry is built on daddy problems! How could you possible know that?" Castiel could not understand what exactly had gone wrong or what was so funny either.

"Common, we better get out of here" Dean said quickly, grabbing Castiel's hand and pulling him out the back door before the security guard could push his way through the crowd of people. The hunter laughed his whole way out and to the Impala, tears threatening to fall from his eyes. They quickly got into the car and drove away.

"Haha, man, Cas. I've had more fun in the one day I've been with you than the whole time I've been with Sammy in a long time" Dean chuckled glancing over at the puzzled angel who still could not grasp what he had done wrong.

They drove on chatting for a few hours. It was now past 2 in the morning and Dean thought it would be a good idea to stop and rest for the night at the next motel they came across.

After checking into a room, the Winchester led the angel into the room, setting his bag on the couch by the door. He cursed loudly as he surveyed the layout of the room. There was a small television against the wall, one bathroom, a table with a couple of chairs, a dusty looking couch, and one bed.

"Dammit. I asked for two beds…" he left the room for a second to talk to the owner, returning seconds later pretty upset. The owner had left the office for the rest of the night assuming that no one else would stop by in the middle of the night looking for a room. They were stuck.

Castiel had been silent since they got out of the car. He stood in the middle of the room, eyes fixed on the bed.

"Cas, you can have the bed. I'll take the…couch" Dean mumbled loud enough for Castiel to hear. When he got no response he stopped unpacking his booze into the small fridge next to the television. He turned to look at the angel who still had not moved an inch since he had step foot into the room.

"Cas, what's wrong?"

"Dean." He replied.

"Yeah?"

"Dean" he repeated.

"Cas, what?" Dean moved to stand infront of the angel. His eyes scanned the angel's for any sign of injury before meeting the piercing blue orbs that belonged to Castiel.

They were silent.

After a few moments Dean dragged his gaze away from the other's mumbling something like "you're acting weird today".

As he turned to get back to what he was doing, Castiel's hand darted out from his sides, grabbing Dean's hand in his own, pulling him back to him. The sheer strength of the angel dragged the full grown man back to his side. Dean lifted one brow in confusion.

"Dean" he paused. "Please tell me what I did wrong back there…Why did that woman run? I don't understand…" the angel admitted.

Dean was silent. He grinned slightly, "It's nothing Cas. She just…had to use the restroom really bad, you know human stuff."

Castiel held his gaze on Dean for a few seconds. He hesitated before asking, "D…does this mean I'm still a virgin?"

Dean bit his lip to keep himself from howling with laughter. The things this angel said he just couldn't take it anymore.

"Yes, haha. From what I saw you didn't get too far with her. We can try again some other time."

"But Dean…I might not be here tomorrow. Rafael will surely destroy me…again."

"Don't say that. I know we were joking around before but don't. You'll be fine. I'll make sure nothing happens to you." Dean could feel his hand clench into a fist.

"There is nothing you can do. He is far too strong for a mere human to do anything."

"Cas-"

"I want you to teach me, Dean."

Dean stared at the angel, mouth hanging slightly open in disbelief. What did this angel just ask him?

"Cas, what th-"

"Dean…" the angel locked his eyes with the older Winchester's. "I…don't think I can trust anyone else with this. I need you to do this for me. Please."

Dean felt a shiver shoot down his spine as the blue eyed angel looked into his eyes. It was as if he were looking straight into his soul. He had only felt this way a few time before this. Each time he did, Castiel had always been asking him for some sort of favor and he could never refuse. Just the other day the angel had convinced him to lend his treasured necklace to him as well. He could not resist then nor could he now.

"…fine" he pulled the angel's body up against his. "Come here."

Dean grunted slightly as the warmth of the angel's body pressed against his own. He swallowed hard, taking a deep breath. He could not believe what he was just about to do. They were both men and Castiel was an angel for heavens sake. This had to be a pretty big sin, not that he cared. What would Sammy think?

"Dean…What should I do?" Castiel muttered, breaking the silence.

"…Kiss me"

**TBC**

A/N: AHHH I'm soooo sorryyyyy I had to end it here haha. I could not write a lemon with all the nonsense at the beginning hahaa. Next chapter will definately be alllllll sexxxxxxx hahaha

Hope you enjoyed. Stay tuned for the next chapter!


	2. We're Far From Done

**Chapter 2: **We're Far From Done

**Disclaimer:** I don't own Supernatural

**Note: **Uhhh....sorry if I get kinda graphic... or if they seem ooc at all. Please let me know if they are!

***

"Dean…What should I do?" Castiel muttered, breaking the silence.

"…Kiss me"

***

"Kiss me, Cas" The hunter growled softly in his deep husky voice.

He allowed his eyes to get lost in the deep ocean of blue that was Castiel, waiting for the other man to react. Castiel stood stiff, eyes wide and shining with a sweet innocence that Dean had always loved about the angel. The hunter chuckled lightly, a smirk painted on his face. He might actually enjoy this.

"I'll show you."

Reaching his hands to grasp the sides of Castiel's face, Dean slowly pulled their faces closer until he could brush his dry lips against the angel's smooth ones. He felt his breathe hitch in his throat. It had been a while since he let anyone get this close to him. Even with all the women he had been sleeping with, it was never this intimate, merely just a series of one night stands and fucking, nothing more.

"Close your eyes."

The angel obeyed silently, leaving himself vulnerable to this Winchester. He sighed softly, lips trembling from the overwhelming feeling of content. Here in this room, he no longer had to be an angel, he no longer had to worry about the apocalypse, he no longer had to be afraid. All that mattered was this moment now, his last moments with Dean.

Letting all his hesitation and thoughts go, Dean pressed his lips against Castiel. Both men could feel a spark shoot to all parts of their body at the softness of the touch. Dean growled deeply, wanting more, needing more.

Even before the angel could register what had happened, Dean had thrown his body onto the bed, ravenously attacking the angel's mouth. His lips tugged and pulled on Castiel's lush pink ones, teeth gently nipping at the sides. Castiel had his eyes shut tight as an intense wave of pleasure washed through his body from his first kiss. It was not every day that an angel could experience such an unholy act.

"C-cas…Open your mouth" Dean panted, hands slowly working their way into Castiel's trench coat.

Again the angel obeyed. He moaned as Dean's tongue darted in and out of his open mouth, tasting every crevice. He felt a slight pressure as Dean licked and sucked on his bruised lips, sending a small jolt to an unfamiliar area in his pants. He coughed slightly, turning his head away from Dean, gasping for air.

Dean snickered, "Was that your first kiss?"

Castiel nodded, chest heaving up and down desperate for air. His face was flushed with a deep shade of pink, lips slightly puffy.

"Mmm…" Dean licked his lips at the delicious sight beneath him. Who knew an angel could ever look so sexy. He leaned over to kiss Castiel again, softly this time, while slowly grinding his hips down against him. Castiel groaned as a burning hot bulge pressed up against his leg.

"D-Dean!"

"Hmm?" Dean hummed in reply before setting out to lick and suck the angel's exposed neck.

"D-Dea..n…" the angel choked out as a new feeling of pleasure shot through his body from the feel of Dean's hot, moist tongue dancing along the skin on his neck. "Dean…I feel weird…Dean!"

"What?" reluctantly Dean lifted his head. He paused to admire the dark red mark on the angel's neck. "What's wrong-"

The angel had his eyes shut tightly, head lying limp to the side, face flushed a deep crimson. Dean was seriously afraid that something bad had happened until he noticed something warm pressing against his inner thigh. He chuckled at how cute the angel was acting and decided he needed to slow down. Castiel had never experienced this before and he probably didn't know what was happening to his body.

Gently, Dean pressed the palm of his hand against the warm bulge in Castiel's pants. He smiled as he felt it jerk slightly at his touch. The angel mewled softly as his body tensed in pleasure. Seeing that the angel liked the new touch, Dean lightly began to rub the angel's hardening member through his pants.

"D-D..Dean..nn" the angel exhaled loudly, clearly enjoy the friction between Dean's hand and own cock.

"How does it feel?" the hunter leaned back over to attack the angel's neck.

"I..don't k-know…" Castiel forced himself to speak before biting down on his lip, turning a loud moan into a deep growl.

Dean had to admit, all this was really turning him on. He could feel his member twitch with curiosity every time a sweet noise escaped the angel's pink lips. At this rate, he was going to explode in his pants if he didn't hurry this up.

Castiel's breath hitched as he felt Dean's wonderful hand begin to unbuckle his belt, skillfully throwing off the angel's pants. Half in a daze, he allowed Dean to slide his trench coat off as well as his button up shirt and tie. He was left panting on the bed, his member fully erect and threatening to rip though his boxers. He watched as Dean tossed the rest of his clothes off of himself, eyes settling on his erection. He swallowed hard, eyes sparkling in slight embarrassment as he looked down at himself.

Dean smirked before pouncing on the angel again. He gave the other a hard kiss before trailing a line of kisses down his neck, his chest, his stomach. He stopped for a moment to tease the hardened nubs on the angel's chest, enjoying the small mewls of pleasure erupt from him. He settled himself between the angel's legs staring at the piece of clothing that separated him from Castiel.

When Dean stopped moving, Castiel hoisted himself up on his elbows to see what was wrong.

"Cas, you ready for this? Are you sure this is what you want?"

The angel gave the hunter a small crooked smile, "Yes."

"Mmm" Dean moaned as his cock jerked at the sight of the angel's incredible smile. It wasn't something you saw everyday after all.

In one swift motion, Dean had the angel's boxers off and halfway across the room. He lowered his head and hovered above the angel's straining erection. He let his hot breath graze the sensitive skin before lapping up the liquid that was dripping down the side. He moaned as Castiel's taste flooded his mouth, he wanted more.

Castiel cringed, gasping harshly as his cock was swallowed by an intense warmth and wetness that was Dean's godly mouth. He choked out the Winchester's name as he threw his head back, falling back onto the bed. He couldn't believe how great it felt to have Dean's mouth on him like this. Now he understood why Dean liked it so much when those women this to him.

Slowly at first, Dean bobbed his head up and down on the angel's member. His cheeks hallowed as he sucked hard. His tongue wrapped around the smooth head of Castiel's cock as he lifted himself off with a loud pop. He growled with lust as he licked his lips, his eyes devouring the angel's body. He couldn't wait anymore. He had to have Castiel.

The angel's breath was coming out in short gasps in an attempt to breathe. Dean brought himself back up to kiss Castiel's forehead. The angel's eyes snapped open shining with bewilderment. Dean couldn't help but smile, pressing his lips onto Castiel's. Their tongues engaged in a battle of dominance as they devoured each other's mouth.

At the same time, Dean had positioned himself above Castiel. He let his body dip slightly, brushing the head of his cock against the angel's. Both the hunter and angel groaned as sparks shot through their bodies. Castiel bucked his hips in an attempt to get the friction he desperately needed from Dean. Dean moaned as he ground his member into the angel's.

They lay there humping each other for a few minutes. Dean could hear the angel's breath quicken. He was close as well. He slipped his hand between their bodies and gripped their member's together, slowly pumping them at the same time.

"D-Dean!" Castiel cried out in a panic. "What's…happenin-"

The angel moaned loudly enough for the people down the hall to hear as he thrust into Dean's hand, shooting his cum onto his chest.

"Fuck!" Dean groaned through gritted teeth as he roughly thrust against the angel. He tensed as he felt himself spill onto the angel's chest. Quickly he brought both his arms up to catch himself from collapsing on his lover for the night.

He opened his eyes a few seconds later, still hazy from the intense orgasm he just had. He felt his cock twitch again at the sight beneath him. Castiel had his eyes clenched tight, mouth slightly opened, cheeks a deep blush, sweat dripping down the side of his face. The angel let his chest fall as he gasped, finally coming down from his first orgasm. It was incredible.

Dean chuckled, "How was it?"

It took Castiel a few more minutes to recover before he could speak, "…Incredible."

Dean smirked and kissed the angel, "We're not done yet."

Castiel's eyes widened as he tilted his head in interest.

"We're far from done, Cas. Ready for round two?"

**TBC**

**A/N: **gahhh I'm soo sorry I'm so evil.. not enough time to finish writing it today. More coming up soon!


	3. Round Two

**Chapter Three:** Round Two

**Note:** None of this belongs to me. Sorry it took so long..

***

"We're far from done, Cas. Ready for round two?"

***

The angel nodded quickly, eager for more of what Dean had to give him. He shivered as the Winchester's hand's slid down his chest, coating his hand with their cum. Castiel watched hungrily as Dean licked the creamy mess off his thumb slowly, before going to lick the rest off his hand. The angel grunted as he felt the warm sensation around his crotch again.

Dean smirked as he leaned forward to kiss Castiel. He pushed his tongue past the angel's parted lips, sliding it against Castiel's own tongue. The angel moaned slightly as his mouth was suddenly filled with a bitter saltiness as they battled for dominance. Both gasping for air, they parted. Dean gave Castiel a longing look as his hazel eyes drowned in the blue ocean of Castiel's.

"Cas…" Dean breathed, a little awkward. He was thinking about how he was going to do this was the angel. He hadn't been with a man before so he was going to have to think this through. He had seen something like this before on the television, two guys going at it with a girl. If he remembered correctly he had to…Oh lord.

Dean laughed nervously letting a small blush cover his cheeks as he thought about what he was about to do. Castiel watched him curiously, getting a little impatient. He slightly thrust upward against Dean, letting his hard cock smear precum on his thigh. Dean shivered at the sudden touch and looked down at Castiel who gave him a small smirk before licking his lips.

"Mmm…Cas."

Quickly, Dean got off the bed and went searching in his bag. Castiel lifted his head silently, watching every movement Dean's muscles made as he bent over revealing his sexy ass to the angel. He growled playfully, urging the hunter to come back to the bed and pay attention to him. He heard a snap as Dean flipped open a bottle of lube and started coating his fingers with it.

"What is that, Dean?" he questioned.

"It...It'll make you feel good, I promise" Dean assured him as he walked over to the bed again. He kneeled onto the bed and moved over Castiel again, kissing him softly.

"This is going to feel a little weird. I promise you that it will feel good, okay? Just bear with me a little bit…" Dean kissed the angel on the forehead.

"I trust you, Dean." Castiel whispered closing his eyes.

Dean took a deep breath and hoped to god he was going to do this right. He pushed the angel's legs upward, exposing his lush ass. He let his lubed fingers gently prod at the angel's entrance, receiving a small mewl of surprise.

"D-Down there?" the angel looked confused.

"Well…We're both guys…It's not really going to go anywhere else…" Dean laughed awkwardly.

Castiel merely tilted his head a little before closing his eyes again. Dean took it as a signal to keep going. He let his fingers gently push against the tight ring of muscles, teasing slightly. Castiel shivered at the feel of the cool gel against his skin, letting a low moan erupt from his throat as he felt the hunter slip the tip of his fingers inside him. Dean gently pushed his finger in deeper until he was enveloped by the tight warmness that was Castiel.

Castiel cringed slightly at the unpleasant feeling as Dean forced his fingers past the tight ring of muscles. He bit his lip tightly, letting his head fall onto its side, as every movement inside him made his stomach lurch with a sudden feeling of tightness. Dean, seeing that this was uncomfortable for the angel, moved down to suck on his exposed neck again, hoping that this would distract him from the pain and discomfort.

"D…ean…" the angel moaned softly at the feel of Dean's hot tongue against his neck, lapping at his speeding pulse.

The hunter bit down on the angel's neck in response trying everything he could to make his partner feel good. After a minute or two, he began to move his fingers in a scissor like motion, spreading Castiel in preparation for what was to come. He thrust his fingers in and out of the angel in a slow but steady motion, being as gentle as he can.

Castiel gasped Dean's name loudly as Dean slipped in a third finger. He was starting to loosen up enough for Dean to bury his fingers up to his knuckles inside him. Dean spread his fingers, reaching upward, searching. This was a little different from fingering a girl, but he knew he was doing something right when the angel cried out in pleasure, back arching off the bed. He smirked. Found it.

"Mmm…Cas…I'm going to fuck you now." Dean moaned in a low voice, pulling his fingers out of the angel. Castiel trembled in need as Dean's warmth left his body. He panted, waiting patiently for Dean to return to him and fill him up. He heard the sound of the bottle opening again.

"Cas…"

The angel heard Dean moan from the foot of the bed. He lazily opened one eye before they both snapped open. He watched as Dean rubbed the lube onto his own cock, rubbing himself in the process. Dean moaned the angel's name as he generously coated himself with lube. He was so turned on by the way the angel's legs were parted and lifted enough for his ass to stick out, almost as if they were begging to be taken.

"Fuck, Cas!" Dean groaned, feeling his climax slowly inch onto him. It took a little effort to pull his hands away, but when he looked as Cas, who was staring at him very intently, licking his lips in interest, he couldn't wait any longer.

Dean got back onto the bed and pushed the angel's legs onto his shoulders, positioning his dick against the angel's opening. Castiel moaned underneath him as he pushed the tip of his cock past the wall of muscle. Dean grunted loudly at the sensation of Castiel's heat swallowing him whole. The angel was so tight, Dean was sure he was going to cum right away. He wanted this to last. He wanted this to last for an eternity.

Dean eyed the angel's hands which were gripping the sheets underneath him. He pulled the angel's arms onto his shoulder, telling him to hold on to him, to scratch him, mark him. Castiel simply stroked the scar he imprinted onto the hunter's shoulder with a content expression. Dean couldn't take any more of this.

He roughly attacked Castiel's mouth as he gently pulled himself out of Castiel, to the tip, before thrusting back in. The angel moaned into the hunter's mouth each time Dean slammed his hard cock back inside of him. He mewled in delight every time Dean thrust in a little deeper, a little harder. He let his fingernails dig into Dean's back as he groaned in pleasure.

Dean was in heaven. He never knew that sex with a man could be so good. Maybe it was just because it was with Cas that it felt good. His head was fuzzy with ecstasy as Castiel's tight ass milked him toward his release. Every sound that left the angel's mouth only turned the hunter on more. He felt it get tighter around his member as Castiel literally hugged Dean's body against his own.

"D…Dean!" he gasped for air.

"Cas…Come…Come for me…" Dean groaned into the angel's ear, slamming into his lover's tight hole harder and faster.

Castiel moaned Dean's name as he was blinded by the bright light of his orgasm, spilling his creamy load onto his own chest. He dragged his nails over Dean's shoulder as he let himself fall back onto the bed trembling from the force of his orgasm. Dean moaned loudly as he watched as the angel orgasm. He could feel the muscles surrounding him clench tightly, throwing the hunter over the edge. He cried out and thrust roughly inside the angel again before shooting his hot cum inside the angel. The angel jerked as he was suddenly filled with a searing heat that was all Dean.

Dean panted heavily, shaking slightly as they struggled to keep him from falling onto the angel. Dean road out the last of his orgasm, watching the angel's beautiful face. He gently placed a kiss on his lips before slowly slipping his softening cock out of his body. Castiel shivered as he felt something warm dribble out between his legs as Dean flopped onto the bed next to him in exhaustion.

They were silent for a few moments in a blissful aftermath of sex. After catching his breath, Dean reached onto the floor for his shirt. He used it to quickly wipe the angel off before tossing it onto the floor again. He reached around Castiel, wrapping his strong arms around him, pulling him against his chest. Castiel silently enjoyed the warmth and the sound of Dean's heartbeat against his ear. He felt so safe in his arms, he never wanted to let go.

"How was it?" Dean asked kissing the angel's sweaty forehead.

Castiel smiled, nuzzling his face against Dean's chest, "Amazing."

Dean smirked, tightening his hold on the angel, "Aren't you glad we didn't spend your last night on earth sitting quietly?"

The angel smiled, merely nodded his head in response, letting his eyes droop in exhaustion. He was glad that he spent his last moments with Dean. He could care less that he was a human, that what they did was sinful. He loved every moment of it, he loved Dean. Dean was his and he was Dean's. It didn't matter if Rafael shredded his body to bits tomorrow. At least he wasn't a virgin anymore.

FIN.

**A/N:** Uhhhh yeahh. So that wasn't as great as I thought it would be..haha I'm better at writing the stuff before this happens haah XD

Hope you all enjoyed it! More coming soon!


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